G6133

L-Glutamic acid γ-(p-nitroanilide) hydrochloride

Name: <SC>L</SC>-Glutamic acid γ-(p-nitroanilide) hydrochloride
Brand: SIGMA
Price: 901 ILS

≥98% (HPLC), glutamine (Gln) transporter alanine-serine-cysteine transporter 2 (ASCT2) blocker, powder

Synonym(s):

L-γ-Glutamyl-p-nitroanilide

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₪3,097.00

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₪8,861.00

₪901.00

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₃N₃O₅ · HCl

CAS Number:

67953-08-6

Molecular Weight:

303.70

EC Number:

267-944-5

MDL number:

MFCD00039054

UNSPSC Code:

12352204

PubChem Substance ID:

24895247

NACRES:

NA.83

Key Documents

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Product Name

L-Glutamic acid γ-(p-nitroanilide) hydrochloride, γ-glutamyl transpeptidase substrate

Assay

≥98% (HPLC)

form

powder

solubility

water: 5 mg/mL, clear, yellow

storage temp.

2-8°C

SMILES string

Cl.NC(CCC(=O)Nc1ccc(cc1)N(=O)=O)C(O)=O

InChI

1S/C11H13N3O5.ClH/c12-9(11(16)17)5-6-10(15)13-7-1-3-8(4-2-7)14(18)19;/h1-4,9H,5-6,12H2,(H,13,15)(H,16,17);1H

InChI key

OJEVFSFTVARWQX-UHFFFAOYSA-N

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Bioactive Small Molecules

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1 of 4

This Item	G1135	49525	G2505
Sigma-Aldrich G6133 L-Glutamic acid γ-(p-nitroanilide) hydrochloride	Sigma-Aldrich G1135 L-Glutamic acid γ-(4-nitroanilide)	Sigma-Aldrich 49525 L-Glutamic acid γ-(3-carboxy-4-nitroanilide) ammonium salt	Sigma-Aldrich G2505 N-Glutaryl-L-phenylalanine p-nitroanilide
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥99.0% (TLC)	assay ≥98% (HPLC)
solubility water: 5 mg/mL, clear, yellow	solubility formic acid: 50 mg/mL, clear to slightly hazy	solubility H₂O: 100 mg/mL, clear, yellow-green	solubility methanol with 1 M NH₄OH: 50 mg/mL, clear to slightly hazy
Quality Level 300	Quality Level 200	Quality Level 200	Quality Level 100
form powder	form powder	form powder	form powder
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C

General description

Substrate for γ-glutamyl transpeptidase

Application

L-Glutamic acid γ-(p-nitroanilide) hydrochloride has been used as a solute carrier family 1 member 5 (SLC1A5) inhibitor:

or an inhibitor of the cell membrane glutamine transporter to study the effects of blocking glutamine uptake on esophageal adenocarcinoma (EACC) and thioredoxin-interacting protein (TXNIP)[1]
in glutamine ELISA assay to treat confluent differentiated uninfected human colonoid monolayer (HCM) in apical and basolateral compartments to study its effects[2]
to study its effect on SLC1A5_var-mediated mitochondrial glutamine transport inhibition[3]
to study its effects on cellular glutathione levels, cellular reactive oxygen species (ROS) levels, and mitochondrial ROS levels[3]

Biochem/physiol Actions

L-Glutamyl-p-nitroanilide (GPNA) is commonly used to block the glutamine (Gln) transporter alanine-serine-cysteine transporter 2 (ASCT2). It can also inhibit sodium-dependent and independent amino acid transporters. GPNA, γ-glutamyltransferase (GGT) substrate plays a key role in the hydrolysis of its γ-glutamyl bond and the subsequent release of the chromogen, p-nitroaniline (PNA).[2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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γ-Glutamyltransferase enzyme activity of cancer cells modulates L-γ-glutamyl-p-nitroanilide (GPNA) cytotoxicity.

Alessandro Corti et al.

Scientific reports, 9(1), 891-891 (2019-01-31)

L-γ-Glutamyl-p-nitroanilide (GPNA) is widely used to inhibit the glutamine (Gln) transporter ASCT2, but recent studies have demonstrated that it is also able to inhibit other sodium-dependent and independent amino acid transporters. Moreover, GPNA is a well known substrate of the

Cross-Talk between Probiotic Nissle 1917 and Human Colonic Epithelium Affects the Metabolite Composition and Demonstrates Host Antibacterial Effect.

Karol Dokladny et al.

Metabolites, 11(12) (2021-12-24)

Colonic epithelium-commensal interactions play a very important role in human health and disease development. Colonic mucus serves as an ecologic niche for a myriad of commensals and provides a physical barrier between the epithelium and luminal content, suggesting that communication

γ-Glutamyltransferase enzyme activity of cancer cells modulates L-γ-glutamyl-p-nitroanilide (GPNA) cytotoxicity.

Alessandro Corti et al.

Scientific reports, 9(1), 891-891 (2019-01-31)

Computational models applied to metabolomics data hints at the relevance of glutamine metabolism in breast cancer.

Lucía Trilla-Fuertes et al.

BMC cancer, 20(1), 307-307 (2020-04-16)

Metabolomics has a great potential in the development of new biomarkers in cancer and it has experiment recent technical advances. In this study, metabolomics and gene expression data from 67 localized (stage I to IIIB) breast cancer tumor samples were

Induction of Thioredoxin-Interacting Protein by a Histone Deacetylase Inhibitor, Entinostat, Is Associated with DNA Damage and Apoptosis in Esophageal Adenocarcinoma.

Paul L Feingold et al.

Molecular cancer therapeutics, 17(9), 2013-2023 (2018-06-24)

In 2017, an estimated 17,000 individuals were diagnosed with esophageal adenocarcinoma (EAC), and less than 20% will survive 5 years. Positron emission tomography avidity is indicative of high glucose utilization and is nearly universal in EAC. TXNIP blocks glucose uptake

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L-Glutamic acid γ-(p-nitroanilide) hydrochloride